Hydrochloric Acid → 2-(4-Fluoro-3-methyl-benzylidene)-hexanoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-butyl-malonic acid (2.319 g, 14.482 mmol), 4-fluoro-3-methylbenzaldehyde (1.000 g, 7.241 mmol), and piperidine (1.232 g, 14.482 mmol) in 10 mL of pyridine was heated to 100° C. and stirred at this temperature for 16 h. After cooling to room temperature, the reaction mixture was poured into 25 mL of concentrated HCl containing 50 g of ice, and then extracted with ethyl acetate. The organic extracts were combined and dried over anhydrous Na2SO4, concentrated under reduced pressure, the product isolated by Flash chromatography (silica gel) eluting with 0-30% ethyl acetate/hexanes to give the title compound as yellow liquid (1.370 g, 80% yield). LC-MS: tR=9.5 min; m/z 237 (M+H)+.

Provenance & Evidence